Triethylamine hydrochloride → HCID 178442550, compound

HRID 1653823Notes

Reaction equation

HRID 1653823 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH3:26])[C:24]#[N:25])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:27]=[N+:28]=[N-:29].[Na+].Cl.C(N(CC)CC)C>CN(C)C=O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([C:24]3[NH:29][N:28]=[N:27][N:25]=3)[CH3:26])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 20080518HCID 20080518, compound

Product 1

HCID 178442550HCID 178442550, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of (RS)-7(4,5-diphenyl-2-oxazolyl)-2-methylheptanenitrile in 30 cm3 of dimethylformamide are treated with twice 1.7 g of sodium azide and twice 3.6 g of triethylamine hydrochloride under the (time and temperature) conditions defined in Example 1. After treatment, the product of the reaction is chromatographed on a column 2 cm in diameter containing 78 g of silica gel (50 to 200μ). The column is eluted, collecting 200 cm3 fractions, with 1 liter of diisopropyl ether and then with 1.6 liters of a diisopropyl ether/ethyl acetate (95:5 by volume) mixture. The fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa). 2.3 g (68%) of (RS)-5-[7-(4,5-diphenyl-2-oxazolyl)-2-heptyl]-1H-tetrazole are obtained in the form of a yellowish oil.

Workup

  1. customAfter treatment, the product of the reaction is chromatographed on a column 2 cm in diameter
  2. additioncontaining 78 g of silica gel (50 to 200μ)
  3. washThe column is eluted
  4. customcollecting 200 cm3 fractions
  5. concentrationThe fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-8165d3b2d32b47ff8317466058bab2cd
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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